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organic compounds 



Acta Crystallographica Section E 

Structure Reports 
Online 

ISSN 1600-5368 

Bis(2-methyl-1H-benzimidazol-3-ium) 
naphthalene-1 ,5-disulfonate 

Shuai-Shuai Wei, a Shou-Wen Jin, a * Qiong Dong, b 
Xin-Chao Cao a and Ze-Yun Yu a 

a Tianmu College of Zhejiang A & F University, Lin'An 31 1 300, People's Republic of 
China, and b Faculty of Science, Zhejiang A & F University, Lin'An 31 1 300, People's 
Republic of China 

Correspondence e-mail: shouwenjin@yahoo.cn 

Received 6 September 2012; accepted 15 September 2012 

Key indicators: single-crystal X-ray study; T = 298 K; mean cr(C-C) = 0.004 A; 
R factor = 0.043; wR factor = 0.1 19; data-to-parameter ratio = 12.5. 



The asymmetric unit of the title compound, 2C 8 H 9 N 2 + -- 
C 10 H 6 O 6 S 2 2 ~, contains a 2-methylbenzimidazolium cation and 
one half of a naphthalene-l,5-disulfonate anion. The formula 
unit is generated by an inversion center. In the crystal, N— 
H- ■ O hydrogen bonds link the components into chains along 
[001]. In addition, weak C— H- ■ O hydrogen bonds and weak 
C— H- ■ -7T interactions are observed. The methyl H atoms 
were refined as disordered over two sets of sites with equal 
occupancy. 

Related literature 

For general background to organic acids, see: Jin et al. (2012); 
Elder et al. (2010); Voogt & Blanch (2005); Wang et al. (2005); 
Zhang et al. (2005). 





Experimental 

Crystal data 

2C 8 HgN 2 + ■ CioH 6 0 6 S2 2 
M, = 552.61 
Triclinic, PI 
a = 8.0360 (7) A 
b = 9.3969 (8) A 
c = 9.5101 (9) A 
a = 105.789 (1)° 
P = 103.303 (1)° 



y = 106.497 (2)° 
V = 624.75 (10) A 3 
Z = 1 

Mo Ka radiation 
fi = 0.26 mm -1 
T = 298 K 

0.45 x 0.41 x 0.19 mm 



Data collection 

Bruker SMART CCD 
diffractometer 

Absorption correction: multi-scan 
(SADABS; Bruker, 2002) 
r mi „ = 0.888, r m „ = 0.951 

Refinement 

R[F 2 > 2a(F 2 )} = 0.043 

wR(F 2 ) = 0.119 

S = 1.05 

2169 reflections 



3137 measured reflections 
2169 independent reflections 
1694 reflections with / > 2a(I) 
R<„, = 0.030 



173 parameters 

H-atom parameters constrained 
Ap max = 0.28 e A~ 3 
Ap mi „ = -0.37 e A~ 3 



Table 1 

Hydrogen-bond geometry (A, °). 

Cgl and Cg2 are the centroids of the C9-Cll/Cll i /C12 i /C13 i and C11-C13/ 
C97C107C11' rings, respectively [symmetry code: (i) —x, —y + 1, — z + 1]. 



D-H-A 


D-H 


H-A 


D- ■ A 


D-H-A 


Nl-Hl-02" 


0.86 


1.86 


2.704 (3) 


165 


N2-H2-01 


0.86 


1.88 


2.684 (3) 


155 


C8-H8E- ■ 03 m 


0.96 


2.32 


3.230 (4) 


158 


C4-H4- ■ Cgl iv 


0.93 


2.61 


3.468 (3) 


154 


C4-H4- ■ Cg2 v 


0.93 


2.61 


3.468 (3) 


154 


Symmetry codes: (ii 
x, y — 1, z — 1. 


x, y, z — 1; (iii) 


-x + l.-y 


+ 1,-2 + 1; (iv) 


— x, — y, — z; (v) 



Data collection: SMART (Bruker, 2002); cell refinement: SAINT 
(Bruker, 2002); data reduction: SAINT; program(s) used to solve 
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine 
structure: SHELXL97 (Sheldrick, 2008); molecular graphics: 
PLATON (Spek, 2009); software used to prepare material for 
publication: SHELXTL (Sheldrick, 2008). 

The authors gratefully acknowledge financial support from 
the Education Office Foundation of Zhejiang Province 
(project No. Y201017321) and the Innovation Project of 
Zhejiang A & F University. 

Supplementary data and figures for this paper are available from the 
IUCr electronic archives (Reference: LH5531). 



References 

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, 
Wisconsin, USA. 

Elder, D. P., Delaney, E., Teasdale, A., Eyley, S., Reif, V. D., Jacq, K., Facchine, 
K. L.. Oestrich, R. S., Sandra, P. & David, F. (2010). J. Pharm. Sci. 99, 2948- 
2961. 

Jin, S. W., Wang, D. Q., Huang, Y. E, Fang, H, Wang, T. Y., Fu, P. X. & Ding, 

L. L. (2012). J. Mol. Struct. 1017, 51-59. 
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
Spek, A. L. (2009). ^Icra Cryst. D65, 148-155. 

Voogt, J. N. & Blanch. H. W. (2005). Cryst. Growth Des. 5, 1135-1144. 
Wang, L., Yu. X. L., Cai, J. W. & Huang, J. W. (2005). J. Chem. Crystallogr. 35, 
481-486. 

Zhang, X. L., Ye, B. H. & Chen, X. M. (2005). Cryst. Growth Des. 5, 1609-1616. 



02964 Wei et al. 



doi:10.1 107/S1 60053681 2039396 



Acta Cryst (2012). E68, o2964 



supplementary materials 



supplementary materials 

Acta Cryst. (2012). E68, o2964 [doi:10.1107/S1600536812039396] 

Bis(2-methyl-1 H-benzimidazol-3-ium) naphthalene- 1 ,5-disulfonate 
Shuai-Shuai Wei, Shou-Wen Jin, Qiong Dong, Xin-Chao Cao and Ze-Yun Yu 

Comment 

Sulfonic acids are important compounds, which have been widely used in various fields as coordination chemistry (Wang 
et al, 2005), pharmaceutical chemistry (Elder et al, 2010), and supramolecular chemistry (Voogt & Blanch, 2005). 
Recently the main focus for sulfonic acids has been in crystal engineering via hydrogen bonded assembly of sulfonic acid 
and organic base (Zhang et al, 2005). As an extension of our study concentrating on hydrogen bonded assemblies of 
organic acids and organic bases (Jin et al, 2012) herein we report the crystal structure of the title compound (I). 

The molecular structure of (I) is shown in Fig. 1. The anion lies across an inversion center. In the crystal, N — H— O 
hydrogen bonds link the components into chains along [001] (Fig. 2). In addition, weak C — H— O hydrogen bonds and 
weak C — H -x interactions are observed. 

Experimental 

2-Methyl-l//-benzimidazole (24.0 mg, 0.20 mmol) was dissolved in 10 ml of methanol, and naphthalene- 1,5-disulfonic 
acid tetrahydrate (36 mg, 0.1 mmol) was added. The solution was stirred for 1 h, and then filtered into a test tube. The 
solution was left standing at room temperature for about one week whereupon colorless block crystals were obtained. 

Refinement 

All H atoms were positioned geometrically with C — H = 0.93-0.96 A, N — H = 0.86 A and constrained to ride on their 
parent atoms with t/i SO (H) = 1.2[/ eq (C,7V). The methyl H atoms were refined as disordered over six sites with equal 
occupancy. 

Computing details 

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 
program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 
(Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: 
SHELXTL (Sheldrick, 2008). 



Acta Cryst (2012). E68, 02964 



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supplementary materials 



02 




Figure 1 

The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Only the 
symmetry unique cation is shown and in the anion unlabeled atoms are related by the symmetry operator (-x, -y+ 1 , -z + 
1). 




Figure 2 

Part of the crystal structure with hydrogen bonds shown as dashed lines. H atoms not involved in the hydrogen bonds 
have been omitted for clarity. 



Acta Cryst. (2012). E68, o2964 



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supplementary materials 



Bis(2-methyl-1 H-benzimidazol-3-ium) naphthalene-1 ,5-disulfonate 



Crystal data 

2C 8 H,N 2 + -C 10 H 6 O 6 S 2 2 - 
M r = 552.61_ 
Triclinic, PI 
Hall symbol: -P 1 
a = 8.0360 (7) A 
b = 9.3969 (8) A 
c = 9.5101 (9) A 
a = 105.789 (1)° 
^= 103.303 (1)° 
y= 106.497 (2)° 
F= 624.75 (10) A 3 

Data collection 

Broker SMART CCD 

diffractometer 
Radiation source: fine-focus sealed tube 
Graphite monochromator 
tp and to scans 

Absorption correction: multi-scan 

(SADABS; Broker, 2002) 
r mm = 0.888, r max = 0.951 



Z= 1 

F(000) = 288 

D x = 1.469 MgnT 3 

Mo Ka radiation, 1 = 0.71073 A 

Cell parameters from 1471 reflections 

6= 2.4-28.0° 

ju = 0.26 mm 1 

T=298 K 

Block, colourless 

0.45 x 0.41 x 0.19 mm 



3 137 measured reflections 
2 1 69 independent reflections 
1694 reflections with/> 2a(T) 
R mt = 0.030 

9imx = 25.0°, 8 min = 2.4° 
h = -9^9 
£ = -8—11 
/ = — 10— ►!! 



Refinement 

Refinement on F 2 

Least-squares matrix: full 

RIF 2 > 2o-( J F 2 )] = 0.043 

wR(F 1 ) = 0.119 

5= 1.05 

2169 reflections 

173 parameters 

0 restraints 

Primary atom site location: structure-invariant 

direct methods 
Secondary atom site location: difference Fourier 

map 



Hydrogen site location: inferred from 

neighbouring sites 
H-atom parameters constrained 
w = U[o\F 0 2 ) + (0.0583P) 2 + 0.1477P] 

where P = (F 0 2 + 2F, 2 )/3 
(A/ f r) max < 0.001 
A/w = 0.28 e A" 3 
A/w = -0.37 e A" 3 

Extinction correction: SHELXL97 (Sheldrick, 

2008), Fc*=kFc [ 1 +0.00 1 xFc 2 l 3 /sin(26»)]- 1/4 
Extinction coefficient: 0.043 (6) 



Special details 

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full 
covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and 
torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. 
An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. 
Refinement. Refinement of F 2 against ALL reflections. The weighted P-factor wR and goodness of fit S are based on F 2 , 
conventional i?-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > aiF 2 ) is used 
only for calculating P-factors(gt) etc. and is not relevant to the choice of reflections for refinement. P-factors based on F 2 
are statistically about twice as large as those based on F, and P-factors based on ALL data will be even larger. 



Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (A 2 ) 



X y Z U ISO */Ueq Occ. (<1) 

Nl 0.2089 (3) 0.0991 (2) -0.0901 (2) 0.0390(5) 

HI 0.1838 0.1027 -0.1817 0.047* 



Acta Cryst. (2012). E68, 02964 



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supplementary materials 



JN2 


0.2562 (3 J 


a 1 £.ih /o\ a k/:i /o\ 

0.1632 (2) 0.1561 (2) 


A A/1 A/1 

0.0404 (5) 




TJ1 

Hz 


0.2664 


A O 1 J O A O J AC 

0.2148 0.2495 


A f\A O * 

0.048* 




Ul 


0.505 / (5) 


A O/IO/I A AC(\A (H\ 

0.2484 (2) 0.4604 (2) 


A ACJA 

0.0530 (6) 




U2 


A 1 C\A C 
0.1946 (5) 


a. i /i 1 o /o\ a 

0.1418 yl) 0.6381 (2) 


A A/1 AH ( Z\ 
0.044/ (5) 




U3 


A /I A 1 A /'I ^ 

0. 41)10 (3 J 


0.4162 (2) 0. /288 (2) 


A ACT A /CA 

0.0524 (5) 




SI 


A Tf ni /o\ 

0.25771 (8) 


0.28337 (7) 0.60043 (6) 


A AOOA /'^\ 

0.0330 (2) 




CI 


0.2166 (4) 


A OAAO /"3\ A ATC/: /T\ 

0.2092 (3) 0.0356 (3) 


0.0383 (6) 




C2 


0.2784 (3) 


A A1 OC /'OX A 1 Azn 

0.0185 (3) 0.1067 (3) 


A A1 C A ( £L \ 

0.0354 (6) 




Lo 


A H AH Z f1\ 

\).Z4 Id \d) 


A ATTA (1\ A AC1 1 /O \ 

— 0.0Z50 (j ) — U.UjH (j) 


a r\i c/i i £\ 
0.03j4 (o) 




C4 


A ^ /"AT / ,1 \ 

0.2607 (4) 


A 1 f 1 /I /OA A 1 IT/' ZO\ 

-0.1614 (3) -0.1376(3) 


A A A 1 £. /T\ 

0.0436 (7) 




TJ A 

H4 


A T2 "7A 

0.23 /y 


a 1 aao n o/iio 
—0.1902 — 0.24.38 


0.052 v 




C5 


A 1 A A C f A \ 

0.3095 (4) 


A IC/II A AC O/l /T\ 

-0.2543 (3) -0.0584 (3) 


A A^Af 

0.0495 (7) 




H5 


0.3 195 


A "1AQ A A 1 IOC 

— 0.34o4 —0.1 12 J 


A A^A* 




/"I s 

C6 


A ^ A A ^ / A\ 

0.3443 (4) 


A^1A^/")\ A1A1A/TN 

-0.2105(3) 0.1010(3) 


A A /I AT / "7 \ 

0.0497 (7) 




H6 


0.3796 


A nf 1 A 1 C f\/~ 

-0.2751 0.1506 


A A/"A;k 

0.060* 




/-in 

C7 


0.3281 (4) 


A AT /I T /I \ A 1 OTA \ 

-0.0747 (3) 0.1870 (3) 


A A /I C C /T\ 

0.0455 (7) 




T T*7 

H7 


A 1 A A'? 

0.3493 


A A/IjCT A 1A1A 

-0.0467 0.2929 


A AC f A 

0.055* 




C8 


A 1 O /" 1 / A\ 

0.1861 (4) 


0.3582 (3) 0.0410 (4) 


0.0552 (8) 




H8A 


0.1993 


0.4176 0.1452 


A A0 1 rfs 

0.083* 


0.50 


Hot> 


A C\£. A J 

0.0643 


0.3332 — 0.026J 


A AOO * 

0.083* 


A CA 

0.50 


H8C 


A A A 

0.2749 


A /10A£ A AATT 

0.4206 0.0077 


A AO * 

0.083* 


A CA 

0.50 


H8D 


a 1 cm 
0.159/ 


A A A^AO 

0.3633 —0.0608 


A AOI * 

0.083* 


A CA 

0.50 


T TOT7 

H8b 


0.2947 


A A A HH A 1 1 (\£i 

0.4477 0.1106 


A AO ") A 

0.083* 


A C A 

0.50 


TUOT7 

Hot 


A AO/1 1 

0.0841 


A 'J/CA'J A A"7 

0.3603 0.0/6/ 


A AC} * 


A CA 

0.50 


C9 


A AA /1 1 f)\ 

-0.0943 (3) 


0.2568 (3) 0.5733 (3) 


A A") C £. 1 £ \ 

0.0356 (6) 




t in 

H9 


a inn 

—0.1013 


A 1 /TOI A f- AAI1 

0.1681 0.6009 


A A A 1 A 

0.043* 




no 


a n^S9 

W.UOJZ \ J J 


A Ck\ f) ^01 (7\ 
U.J4ZV ^ J ) \j.DDyi \Z) 


U.WZoH- \J ) 




Cll 


0.0793 (3) 


0.4782 (3) 0.5137 (2) 


0.0275 (5) 




C12 


0.2405 (3) 


0.5702 (3) 0.4963 (3) 


0.0336 (6) 




H12 


0.3438 


0.5427 0.5143 


0.040* 




C13 


0.2477 (3) 


0.6986 (3) 0.4535 (3) 


0.0388 (6) 




H13 


0.3552 


0.7570 0.4421 


0.047* 




Atomic displacement parameters (A 2 ) 






JJ12 JJii JJ12 


LP 3 


IP 


Nl 


0.0449(13) 


0.0439 (13) 0.0288 (11) 0.0159 (11) 


0.0095 (10) 


0.0171 (10) 


N2 


0.0476 (14) 


0.0419(13) 0.0294(11) 0.0160(11) 


0.0130(10) 


0.0101 (10) 


01 


0.0700(14) 


0.0829(15) 0.0407(11) 0.0547 (12) 


0.0338 (10) 


0.0335 (10) 


02 


0.0573 (12) 


0.0481 (11) 0.0447(10) 0.0312 (10) 


0.0162 (9) 


0.0290 (9) 


03 


0.0407(11) 


0.0512 (12) 0.0517(12) 0.0217(10) 


-0.0051 (9) 


0.0104(9) 


SI 


0.0378 (4) 


0.0441 (4) 0.0266(3) 0.0251 (3) 


0.0108 (3) 


0.0166 (3) 


CI 


0.0355 (14) 


0.0395 (15) 0.0375 (14) 0.0113 (12) 


0.0089 (11) 


0.0155 (12) 


C2 


0.0355 (14) 


0.0385 (14) 0.0301 (13) 0.0099 (11) 


0.0107(11) 


0.0136(11) 


C3 


0.0368 (14) 


0.0395 (14) 0.0319 (13) 0.0130(12) 


0.0118(11) 


0.0166(11) 


C4 


0.0476(17) 


0.0448 (16) 0.0327 (13) 0.0148 (13) 


0.0114(12) 


0.0095 (12) 


C5 


0.0500(17) 


0.0393 (16) 0.0580(18) 0.0182 (14) 


0.0170(15) 


0.0149(14) 


C6 


0.0512(18) 


0.0452 (17) 0.0570(18) 0.0174(14) 


0.0127 (14) 


0.0298 (15) 


C7 


0.0518(17) 


0.0488 (17) 0.0369 (14) 0.0144 (14) 


0.0125 (13) 


0.0235 (13) 


C8 


0.0558 (19) 


0.0448 (17) 0.0609(19) 0.0220(15) 


0.0107(16) 


0.0169(15) 


/\cta Gyst. (2012). E68, o2964 






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supplementary materials 



C9 


0.0424 (15) 


0.0397 (14) 


0.0350 (13) 


0.0185 (12) 


0.0167(12) 


0.0221 (12) 


CIO 


0.0315 (13) 


0.0366 (13) 


0.0225 (11) 


0.0181 (11) 


0.0092 (10) 


0.0126(10) 


Cll 


0.0318(13) 


0.0336 (13) 


0.0214(11) 


0.0162(11) 


0.0100(10) 


0.0112(10) 


C12 


0.0286(13) 


0.0467 (15) 


0.0353 (13) 


0.0211 (12) 


0.0137(11) 


0.0194(12) 


C13 


0.0329 (14) 


0.0477 (15) 


0.0463 (15) 


0.0160(12) 


0.0194(12) 


0.0261 (13) 



Geometric parameters (A, °) 



Nl— CI 


1.327 (3) 


C6— H6 


0.9300 


Nl— C3 


1.390 (3) 


C7— H7 


0.9300 


Nl— HI 


0.8600 


C8— H8A 


0.9600 


N2— CI 


1.335 (3) 


C8— H8B 


0.9600 


N2— C2 


1.389 (3) 


C8— H8C 


0.9600 


N2— H2 


0.8600 


C8— H8D 


0.9600 


01 — SI 


1.4491 (17) 


C8 — H8E 


0.9600 


02— SI 


1.4543 (17) 


C8— H8F 


0.9600 


03— SI 


1.4427(19) 


C9— CIO 


1.366 (3) 


SI— CIO 


1.786 (2) 


C9— CI 3' 


1.403 (4) 


CI— C8 


1.478 (4) 


C9— H9 


0.9300 


C2— C3 


1.386 (3) 


CIO— Cll 


1.433 (3) 


C2— C7 


1.390 (4) 


Cll— C12 


1.413 (3) 


C3— C4 


1.384 (3) 


Cll— Cll 1 


1.436 (4) 


C4— C5 


1.378 (4) 


C12— C13 


1.365 (3) 


C4— H4 


0.9300 


C12— H12 


0.9300 


C5— C6 


1.395 (4) 


CI 3— C9 1 


1.403 (4) 


C5— H5 


0.9300 


C13— H13 


0.9300 


C6— C7 


1.375 (4) 






CI— Nl— C3 


109.56(19) 


H8A— C8— H8B 


109.5 


CI— Nl— HI 


125.2 


CI— C8— H8C 


109.5 


C3— Nl— HI 


125.2 


H8A— C8— H8C 


109.5 


CI— N2— C2 


109.1 (2) 


H8B— C8— H8C 


109.5 


CI— N2— H2 


125.5 


CI— C8— H8D 


109.5 


C2— N2— H2 


125.5 


H8A— C8— H8D 


141.1 


03— SI— 01 


112.92(13) 


H8B— C8— H8D 


56.3 


03— SI— 02 


113.16(11) 


H8C— C8— H8D 


56.3 


01— SI— 02 


111.54(11) 


CI— C8— H8E 


109.5 


03— SI— CIO 


106.00(11) 


H8A— C8— H8E 


56.3 


01— SI— CIO 


106.50(10) 


H8B— C8— H8E 


141.1 


02— SI— CIO 


106.07(11) 


H8C— C8— H8E 


56.3 


Nl— CI— N2 


108.8 (2) 


H8D— C8— H8E 


109.5 


Nl— CI— C8 


125.5 (2) 


CI— C8— H8F 


109.5 


N2— CI— C8 


125.7 (2) 


H8A— C8— H8F 


56.3 


C3— C2— N2 


106.4 (2) 


H8B— C8— H8F 


56.3 


C3— C2— C7 


121.8 (2) 


H8C— C8— H8F 


141.1 


N2— C2— C7 


131.7 (2) 


H8D— C8— H8F 


109.5 


C4— C3— C2 


121.7 (2) 


H8E— C8— H8F 


109.5 


C4— C3— Nl 


132.2(2) 


010^9—013' 


120.3 (2) 


C2— C3— Nl 


106.1 (2) 


CIO— C9— H9 


119.8 


C5— C4— C3 


116.6(2) 


013^9—^ 


119.8 



Acta Cryst. (2012). E68, 02964 



sup-5 



supplementary materials 



C5 — C4 — H4 


121.7 




C9 — C10 — Cll 




121.2 (2) 


C3 — C4 — H4 


121.7 




/""i A 1 A CM 

C9 — C10 — SI 




118.13 (18) 


f • A Of p / 

C4 — C5 — Co 


1 O 1 C /") \ 

121. 5 (3) 




pi 1 P 1 (\ Ol 

Cll — C10 — SI 




1 OA /"I / 1 "7\ 

120.63 (17) 


r • A p C TTf 

C4 — C5 — H5 


119. 2 




pm o n i f ' i a 

C 1 2 — C 1 1 — C 1 U 




123.4 (2) 


Co — C5 — H5 


1 1 a o 

119.2 




nil i /"M 1 i 

C12 — Cll — Cll 




1 1 O A /1\ 

118.9 (2) 


C7 — Co — C5 


122.0 (3) 




C10 — Cll — Cll 




117.7(3) 


/~n /■ < / tt/' 

C7 — Co — Ho 


1 1 a a 

119.0 




P1 O p 1 P 1 1 

C13 — C12 — Cll 




12 1. 3 (2) 


C5— C6— H6 


119.0 




C13— C12— H12 




119.4 


C6— C7— C2 


116.2 (2) 




Cll— C12— H12 




119.4 


C • / f~^H T T "7 

Co — C7 — H7 


121.9 




p i o /-in /"<Ai 

C12 — C13 — C9 




1 OA C /0\ 

120.5 (2) 


C2 — C7 — H7 


ni a 

121.9 




pn pn Tin 

C12 — C13 — H13 




119.7 


C • 1 /-i o TTO A 

C 1 — C8 — H8A 


109.5 




C9 — C13 — H13 




119.7 


/"M f" 1 o i ion 

C 1 — C o — HoB 


109.3 










C3 — N 1 — C 1 — N2 


-1.0 (3) 




C3 — C2 — C7 — C6 




-0.2 (4) 


/~1 O \T1 p 1 po 

C3 — Nl — CI — C8 


1 "7 A 1 /O \ 

179.1 (3) 




N2 — C2 — C7 — C6 




-177.4 (3) 


C2 — Nz — C 1 — JN 1 


1.1 (3) 




C 13 — C9 — C 1 0 — C 1 1 




-1.3 (4) 


C2 — JN 2 — C 1 — C o 


1 "70 n \ 

-178.9 (3) 




/"M^i p A p 1 A CI 

C 13 1 — C9 — C 1 0 — S 1 




1 to in /i o\ 

178.19 (18) 


C 1 — N2 — C2 — C3 


-0.9 (3) 




03 — S l — C 1 0 — C9 




-118.6 (2) 


C 1 — N 2 — C2 — C7 


176.6 (3) 




f~\ 1 CI /"MA p A 

Ol — SI — C10 — C9 




1 OA A ZO\ 

120.9 (2) 


mo n n /~m 
IN 2 — C2 — C3 — C4 


1 /9.3 (2) 




U2 — S 1 — C 1 0 — C9 




2.0 (z) 


C7 — C2 — C3 — C4 


1.5 (4) 




03 — S 1 — C 1 0 — C 1 1 




^A A 

60.9 (2) 


~k to r"i /"■""> \ti 

N2 — C2 — C3 — N 1 


0.3 (3) 




Ol — SI — C10 — Cll 




-59.6 (2) 


C7 — C2 — C3 — N 1 


-177.5 (2) 




/ \ CM f " 1 A pi 1 

02 — S 1 — C 1 0 — C 1 1 




1 no C A { 1 T\ 

-178.54 (17) 


pi xti /~m 
CI — JN 1 — C3 — C4 


1 HQ A t1\ 

— 1 /8.4 (3) 




C9— C10— Cll— C12 




— 1 /9.5 (z) 


1^1 IN 1 V^Z 






SI— C10— Cll— C12 




1 1 (X\ 


C2— C3— C4— C5 


-1.2 (4) 




C9— C10— Cll— Cll 1 




1.1 (4) 


Nl— C3— C4— C5 


177.5 (3) 




SI— C10— Cll— Cll' 




-178.4(2) 


C3— C4— C5— C6 


-0.2 (4) 




C10— Cll— C12— C13 




-179.7(2) 


C4— C5— C6— C7 


1.4 (5) 




Cll 1 — Cll— C12— C13 


-0.2 (4) 


C5— C6— C7— C2 


-1.2 (4) 




Cll— CI 2— CI 3— C9 1 




0.4 (4) 


Symmetry code: (i) -x, -y+\, -z+1. 












Hydrogen-bond geometry (A, °) 












Cgl and Cg2 are the centroids of the C9-C11/C11VC 127013' and Cll-Cn/C^/ClOVCl!' rings, respectively [symmetry code: (i) -x, -y + 1, -z + 1] 


D—R-A 




D — H 


R-A 


D-A 


D—R-A 


Nl— HI -02" 




0.86 


1.86 


2.704 (3) 


165 


N2— H2-01 




0.86 


1.88 


2.684 (3) 


155 


C8— RSE03 m 




0.96 


2.32 


3.230(4) 


158 


C4— H4-Cgl lv 




0.93 


2.61 


3.468 (3) 


154 


C4— H4-Cg2 v 




0.93 


2.61 


3.468 (3) 


154 



Symmetry codes : (ii) x, y, z- J ; (iii) -x+ 1 , -y+ 1 , -z+ 1 ; (iv) -x, -y,-z;{\)x,y-\,z-\. 



Acta Cryst. (2012). E68, 02964 



sup-6